USAA just performed an on-site inspection of our personal residence as standard procedure for certain new policies and they REDUCED our premium from the original quote/price.  

If your goal is to reduce that self-employment tax to a minimum, an S Corporation is the best entity to use.

The reason I want to split the properties is because I want introduce business process and reduce my person dependencies.

If so, your capex expenditures would be greatly reduced although that is usually offset by the HOA fees you will pay.Request copies of the By-Laws and Declarations and read them thoroughly so you can have a firm grasp on what you are responsible for and what the HOA is responsible for.

You'll also need to have reserves ( about 6 months worth) of PITI for the subject property as well as the one you already own and pay off any credit card debt you have to reduce debt to income ratio.

Students who wish to pursue a higher degree down the line may be discouraged to do so because of the already crippling debt they have acquired which could end up reducing the amount of people willing to gain a higher degree due to the additional cost.

With freeze thaw it will keep you from getting patches of ice or at least greatly reduce them.

Under stairs and reduce storage room under stairs.

I also like the idea your sister did with reducing inheritance by a value equal to the property. 

It's unlikely you will mitigate W-2 earnings as passive income (rental activity) won't reduce your w-2 income tax liability.As for replacing the AC.